Chapter 2
Advanced Problems in Organic Chemistry for Competitive Examinations · 59 exercises
Problem 5
The total number of structural isomers of \(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\) would be (a) 4 (b) 8 (c) 5 (d) 10
6 step solution
Problem 7
How many geminal dichloride with different formula are possible for \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}\) ? (a) only one (b) two (c) three (d) four
5 step solution
Problem 8
What is the relation between 3-ethylpentane and 3-methylhexane? (a) Chain isomers (b) Position isomers (c) Functional isomers (d) Metamers
5 step solution
Problem 10
The compounds \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) represent (a) chain isomerism (b) position isomerism (c) functional isomerism (d) all of the above
5 step solution
Problem 11
An isomer of ethanol is (a) methanol (b) acetone (c) diethyl ether (d) dimethyl ether
7 step solution
Problem 12
The number of primary, secondary and tertiary amines possible with the molecular formula \(\mathrm{C}_{3} \mathrm{H}_{9} \mathrm{~N}\) respectively (a) \(1,2,2\) (b) \(1,2,1\) (c) \(2,1,1\) (d) \(3,0,1\)
5 step solution
Problem 16
Identify specific rotation of a mixture have \(5 \mathrm{~g}\) of \((+) 2\) -butanol and \(7 \mathrm{~g}\) of \((-) 2\) -butanol (If specific rotation of \(100 \%\) pure compound is \(13.5^{\circ}\) ) (a) \(-2.25^{\circ}\) (b) \(-1.6^{\circ}\) (c) \(12.2^{\circ}\) (d) \(4.45^{\circ}\)
6 step solution
Problem 17
Which compound is not the isomer of 3 -ethyl-2-methylpentane?
3 step solution
Problem 24
Identify compounds that give geometrical isomerisation
4 step solution
Problem 25
Which conformation has a \(\mathrm{C}_{3}\) axis of symmetry? (a) Boat (b) Twist boat (c) Chair (d) Enveloped
3 step solution
Problem 26
Which of the following can show tautomerism? (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CNO}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (c) \(\mathrm{R}_{3} \mathrm{CNO}_{2}\) (d) \(\mathrm{RCH}_{2} \mathrm{NO}_{2}\)
4 step solution
Problem 28
Choose the total number of constitutional isomers with the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\). (a) 9 (b) 7 (c) 5 (d) 3
7 step solution
Problem 28
Which will not show tautomerism? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NO}_{2}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{NO}_{2}\) (c) (d) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{NO}_{2}\)
5 step solution
Problem 29
Which of the following compound show tautomerism?
(a) \(\left(\mathrm{H}_{3} \mathrm{C}\right)_{2}
\mathrm{CCl}-\mathrm{CH}=\mathrm{CH}_{2}\)
(b)
3 step solution
Problem 30
In which structure Gauche form has less potential energy than antiform (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}+\mathrm{CH}_{2}-\mathrm{Cl}\) (b) \(\mathrm{HO}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{F}\) (c) \(\mathrm{CH}_{2}\) ) \(\mathrm{CH}_{2}\) (d) \(\mathrm{HO}-\mathrm{CH}_{2}+\mathrm{CH}_{2}-\mathrm{OH}\)
4 step solution
Problem 31
Tautomerism will be exhibited by (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CNO}\) (c) \(\mathrm{R}_{3} \mathrm{CNO}_{2}\) (d) \(\mathrm{RCH}_{2} \mathrm{NO}_{2}\)
6 step solution
Problem 32
Which of the following is not an example of tautomeric equilibrium? (a) \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{C}=\mathrm{O} \rightleftharpoons \mathrm{CH}_{2}-\mathrm{CH}=\mathrm{C}-\mathrm{O}\) (b) \(-\mathrm{N}=\mathrm{N}-\mathrm{NH} \rightleftharpoons \mathrm{NH}-\mathrm{N}=\mathrm{N}\) (c) \(>\mathrm{CH}-\mathrm{N}=\mathrm{O} \rightleftharpoons>\mathrm{C}=\mathrm{N}-\mathrm{OH}\) (d) \(-\mathrm{NH}-\mathrm{C}=\mathrm{O} \rightleftharpoons-\mathrm{N}=\mathrm{C}-\mathrm{OH}\)
6 step solution
Problem 37
Geometrical isomers differ in (a) position of functional group (b) spatial arrangement of atoms (c) position of atoms (d) length of carbon chain
3 step solution
Problem 38
Stereoisomers have different (a) Molecular formula (b) Structural formula (c) Configuration (d) Molecular mass
5 step solution
Problem 41
Which compound can show geometrical isomerism? (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\)
5 step solution
Problem 50
The number of geometrical isomers in the following compound is \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{C}_{2} \mathrm{H}_{5}\) (a) 4 (b) 3 (c) 2 (d) 5
4 step solution
Problem 52
Identify compound(s) in which gauche conformer is more stable than staggered (a) 1,2 -difluoroethane (b) Chloropropane (c) Ethylene glycol (d) Succinic acid
5 step solution
Problem 52
What characteristic is the best common to both cis-2-butene and trans-2-butene? (a) B.P. (b) Dipole moment (c) Heat of hydrogenation (d) Product of hydrogenation
5 step solution
Problem 58
The number of optically active compounds in the isomers of \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Br}\) is (a) 1 (b) 2 (c) 3 (d) 4
4 step solution
Problem 60
The number of optically active isomers observed in 2,3 -dichlorobutane is (a) 0 (b) 2 (c) 3 (d) 4
5 step solution
Problem 64
The instrument which can be used to measure optical activity, i.e., specific rotation (a) Refractometer (b) Photometer (c) Voltmeter (d) Polarimeter
3 step solution
Problem 72
Identify the structure of Erythro-butane-2, 3-diol
5 step solution
Problem 73
The enantiomeric excess and observed specific rotation of a mixture containing \(6 \mathrm{~g}\) of \((+)-2\) -butanol and \(4(\mathrm{~g})\) of \((-)-2\) -butanol are respectively (If the specific rotation of enantiomerically pure \((+)-2\) -butanol is \(+13.5\) units) (a) \(80 \%\), \(+2.7\) unit (b) \(20 \%,-27\) unit (c) \(20 \%,+2.7\) unit (d) \(80 \%\), \(-27\) unit
5 step solution
Problem 74
Which of the following pair of isomers cannot be separated by fractional
crystallisation or fractional distillation?
(a) Maleic acid and fumaric acid
(b) (+)-Tartaric acid and meso-tartaric acid (c)
\(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{COOH}\) and \(\mathrm{H}_{2}
\mathrm{~N}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{COOH}\)
7 step solution
Problem 75
Increasing order of stability among the three main conformation (i.e., eclipse, anti, gauche) of ethylene glycol is (a) Eclipse, gauche, anti (b) Gauche, eclipse, anti (c) Eclipse, anti, gauche (d) Anti, gauche, eclipse
5 step solution
Problem 79
In the Newman projection formula of the least stable staggered form of \(\mathrm{n}\) -butane, which of the following reasons is the causes of its unstability? (a) Van der Waal's strain (b) Torsional strain (c) Combination of both (d) None of these
4 step solution
Problem 81
The dihedral angle between two methyl groups in partially eclipsed conformation of n-butane is (a) \(180^{\circ}\) (b) \(120^{\circ}\) (c) \(90^{\circ}\) (d) \(109^{\circ} 28^{\prime}\)
3 step solution
Problem 84
Evaporation of an aqueous solution of ammonium cyanate gives urea. This reaction follows the class of (a) Polymerisation (b) Isomerisation (c) Association (d) Dissociation
4 step solution
Problem 85
The possible number of alkynes with the formula \(\mathrm{C}_{5} \mathrm{H}_{8}\) is (a) 2 (b) 3 (c) 4 (d) 5
4 step solution
Problem 86
How many isomers of \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{OH}\) will be primary alcohols (a) 2 (b) 3 (c) 4 (d) 5
4 step solution
Problem 87
Identify the compounds that give trans product on reaction with alcoholic KOH and heat
6 step solution
Problem 87
Number of isomeric forms of \(\mathrm{C}_{7} \mathrm{H}_{9} \mathrm{~N}\) having benzene ring will be (a) 7 (b) 6 (c) 5 (d) 4
5 step solution
Problem 88
Which of the following is an isomer of diethyl ether (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (b) \(\mathrm{CH}_{3} \mathrm{CHO}\) (c) \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}\) (d) \(\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{CHOH}\)
4 step solution
Problem 89
Total number of isomeric alcohols with the formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) is (a) 1 (b) 2 (c) 3 (d) 4
5 step solution
Problem 90
Different spatial arrangements of the atom that result from restricted rotation about a single bond are conformers. The general stability order of these conformer are as follows. Anti \(>\) Gauch \(>\) Partially eclipsed \(>\) Fully eclipsed Although anti is more stable than gauch but in some cases gauch is more stable than anti. Number of possible stable conformers of butane is (a) 2 (b) 4 (c) 6 (d) Infinite
4 step solution
Problem 90
The molecular formula of a saturated compound is \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{Cl}_{2}\). The formula permits the existence of two (a) functional isomers (b) position isomers (c) optical isomers (d) cis-trans isomers
5 step solution
Problem 91
The type of isomerism found in urea molecule is (a) Chain (b) Position (c) Tautomerism (d) None of these
4 step solution
Problem 92
An alkane can show structural isomerism if it has ......... number of minimum carbon atoms (a) 1 (b) 2 (c) 3 (d) 4
5 step solution
Problem 93
How many chain isomers can be obtained from the alkane \(\mathrm{C}_{6} \mathrm{H}_{14} ?\) (a) 4 (b) 5 (c) 6 (d) 7
5 step solution
Problem 97
In the reaction: \(\mathrm{CH}_{3} \mathrm{CHO}+\mathrm{HCN} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CN}\) a chiral centre is produced. The number of stereoisomers of the product is (a) 3 (b) 2 (c) 4 (d) none of these
4 step solution
Problem 98
Among the following conformers, which has highest potential energy for \(\mathrm{n}\) -butane (along \(\mathrm{C}_{2}-\mathrm{C}_{3}\) bond rotation)? (a) Skew (b) Fully eclipsed (c) Staggered (d) Partially eclipsed
4 step solution
Problem 98
The molecule 3 -penten-2-ol can exhibit (a) Optical isomerism (b) Geometrical isomerism (c) Metamerism (d) Tautomerism The correct answer is (a) (a) and (b) (b) (a) and (c) (c) (b) and (c) (d) (a) and (d)
6 step solution
Problem 99
Find the total number of isomers (including stereo isomers) in dimethyl cyclopropane and dimethyl cyclobutane (a) 6,8 (b) 5,6 (c) 4,5 (d) 4,6
3 step solution
Problem 104
Racemic mixture is formed by mixing two (a) Isomeric compounds (b) Chiral compounds (c) Meso compounds (d) Enantiomers
3 step solution
Problem 105
Which of the following does not show geometrical isomerism? (a) 1,2 -dichloro-1-pentene (b) 1,3 -dichloro-2-pentene (c) 1,1-dichloro-1-pentene (d) 1,4 -dichloro-2-pentene
6 step solution